


Castiel’s Guide to Wooing a Winchester

by exmanhater



Category: Supernatural
Genre: M/M, Podfic Available
Language: English
Status: Completed
Published: 2010-12-02
Updated: 2010-12-02
Packaged: 2017-10-18 09:18:35
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,620
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/187338
Author URL: https://archiveofourown.org/users/exmanhater/pseuds/exmanhater
Summary: <blockquote class="userstuff">
              <p>Castiel had never doubted that he was meant for Dean. Getting Dean to see it proved another matter entirely.</p>
            </blockquote>





	Castiel’s Guide to Wooing a Winchester

**Author's Note:**

> Written for the fourth round of Secret Angels at [deancastiel](http://community.livejournal.com/deancastiel), originally posted [there](http://community.livejournal.com/deancastiel/2547890.html)

**1\. Do not, under any circumstances, use the word _woo_**

 

“What is that?” Dean asked with a confused expression.

Castiel looked down at the flowers in his hands. It seemed quite obvious to him, but perhaps Dean did not come into contact with bouquets often enough to know what they were. “Flowers,” he told Dean, still holding the bouquet out for Dean to take.

“Yeah, I got that, but why are you giving them to me?”

Castiel frowned. “Is that not what I should do to show you my intentions?” he asked, ignoring Sam’s disbelieving snort of laughter from the other side of the room.

Dean’s mouth dropped open. Castiel made a mental note to make Dean’s mouth drop open more often. It was an extremely pleasing sight.

“Intentions?” Dean asked warily. “Intentions to do what?”

“Woo you,” Castiel replied, somewhat bemused. He had thought his affections for Dean were quite easy to see. Certainly, all of his brothers had noticed the danger long before Castiel himself had, and they were not the most emotionally aware bunch around.

Sam, now in danger of choking he was laughing so hard, made his way to the door as Dean spluttered in shock. “I’m, I’m going to go – um, somewhere,” Sam said, closing the door of the motel room behind him. Castiel nodded a goodbye to Sam, grateful for his foresight. If this progressed the way he hoped it would, he and Dean would require privacy.

Turning back to Dean, Castiel admired his blushing face and watched his Adam’s apple move up and down in his throat as he swallowed.

“Uh, Cas,” Dean finally said, carefully taking the flowers from Castiel’s hands and setting them on the nightstand. “Did you come into contact with any cupids recently? Or a trickster?”

Castiel shook his head firmly. Dean clearly did not understand the situation at all. “No,” he said, “but even if I had, it would not have anything to do with my desire to court you.”

Dean blushed again. “Are you serious?” he asked. “You want to what, date me?”

Castiel considered the word and rejected it as too simplistic. “No,” he said, quickly adding, “I think I would like to pursue something much more permanent with you than dating.”

Dean sat down on the bed in a rush, as if his legs had grown too weak to stand. “Uh, okay,” he said, and then he grabbed a bottle of holy water from the nightstand drawer and dumped it all over Castiel.

Castiel stared at Dean in reproach as he willed away the water. “If you do not want my attentions, you can just tell me,” he said stiffly, moving toward the door in preparation to leave. He had not considered Dean a sure thing, but he had thought there was a good chance Dean would return his feelings. They had made a connection unlike any other Castiel had experienced, and he was certain it was not completely one-sided.

Dean sighed. “Don’t go, Cas, I’m sorry, I’m just surprised that you – that you like me, I guess.”

Castiel walked back to the bed and sat next to Dean. “Why would that surprise you?” he asked. “I think I’ve been fairly obvious about it.”

Dean placed a hand on Castiel’s arm, and the warmth of it burned pleasantly. “I just, I just didn’t see things the same way you did,” Dean said. “Can you give me some time to think about it?”

Castiel reached out and ran a hand down Dean’s neck to his shoulder, relishing the shudder that went through Dean at the touch. “Of course,” he said. “I will see you later.”

Dean smiled, finally, and nodded as Castiel stood.

“Just, uh, a word of advice?” Dean said, a second before Castiel disappeared. “Don’t say “woo” or “court” unless you want me to laugh in your face, okay?”

 

**2\. Employ the help of friends and/or family**

 

“Sam,” Castiel said solemnly, after he knocked politely and waited for Sam to let him enter the room instead of directly appearing inside with no warning. “I have a very important question for you.”

Sam, wearing an expression Castiel could not quite parse (it seemed like confusion, but it wasn’t), pushed a hand through his hair and said, “okay, shoot.”

Castiel ignored the ridiculous idiom. “I need your blessing on my relationship with Dean. He would not be happy unless you got along with his partner, and while I believe you and I have formed a friendship, I don’t know what you think of me as a potential brother-in-law.”

Sam gaped, and Castiel wished privately that he had known about this method of getting Winchesters to shut up earlier, when it would have saved a good deal of trouble.

“Wow,” Sam said eventually. “So you’re really serious about this wooing thing?”

Castiel nodded. “But please don’t call it that – Dean has expressed his displeasure with the term.”

“Of course he did,” Sam said in a strangled voice. “Well, it’s really up to Dean, you know that, right?”

“Yes,” Castiel replied, “but I believe your approval will allow him to make the decision more easily. If he isn’t worried about what you might think, a significant obstacle will be removed.”

“That’s – that’s really thoughtful,” Sam said, still sounding vaguely choked up. “I’ll let him know I don’t have any problems with him hooking up with you.”

“Thank you,” Castiel said, and made a move toward the door.

“Wait,” Sam said, looking a little embarrassed. “You totally have my blessing, okay? Just don’t tell Dean I said that or we’ll both be in trouble for making decisions without his input.”

Castiel felt a sudden surge of brotherly affection for Sam. “Of course,” he said, “thank you, again.”

“And, uh, you might want to try bribing him with pie,” Sam added. “That usually works for me.”

 

**3\. Always keep your Winchester wanting more**

 

The next time Castiel saw Dean, he could tell that Sam had been true to his word. Dean seemed less worried about Castiel’s proposal and more willing to include Castiel in the non-hunting parts of his life. Along with Sam, they spent many evenings watching TV to get Castiel educated in pop culture, and Dean frequently sought Castiel’s company for things like getting supplies or having lunch at a restaurant.

Today they were relaxing after a simple ghost exorcism. Castiel had planned ahead and arranged with Sam for some time alone in the motel room, and had cherry pie waiting for Dean when they arrived. Dean had eaten it with gusto and loud noises. Castiel had watched and tried not to seem as aroused as he was by the sight and sound of Dean enjoying something so physically.

Now they sat across from each other at the tiny dinette table, content with silence.

After a moment, however, Dean looked up. “You’re not so bad at this dating thing,” he said.

“Is it dating?” Castiel asked. “The last time we talked, you still did not seem sure about that.” He himself did not really want to call it dating, since as far as he was concerned he would never want anyone other than Dean, but it helped Dean to call it dating, so he didn’t object.

Dean smiled, a new smile that Castiel had never seen before. It quickened the blood in his veins and made him take an unnecessary breath.

“Yeah,” Dean said, “it’s dating.”

“Oh,” Castiel replied, caught off balance at reaching his goal so suddenly. Then a thought occurred and he stood and moved to the bed, pulling Dean along with him until they were both seated next to each other on the lumpy mattress.

Castiel leaned in close to Dean and placed a hand on his neck. “I believe dating usually involves quite a bit of physical contact,” he said softly, watching Dean’s pupils expand.

“Yeah,” Dean replied, leaning into Castiel’s hand. Castiel took this as a sign and placed a soft kiss at the corner of Dean’s mouth, deepening it into a real kiss when Dean sighed and relaxed into Castiel’s hold, opening his lips and welcoming the touch. Castiel kept pushing, unable to get enough of the taste of Dean’s mouth, moving his tongue in slow swipes inside, biting Dean’s lips when he could manage it. Dean let him do as he wanted for long, long moments, hands on Castiel’s shoulders, holding him close and making delicious noises.

Castiel could have done this forever, but he came back to himself when Dean moved a hand to his crotch. He caught the hand and broke the kiss, shaking his head.

“No, no,” he whispered, “not yet.” Dean leapt back out of his hold as if stung, and Castiel realized his mistake and took Dean’s hands back into his.

“I want to,” he said roughly, aware of how wild he must look, if Dean’s flushed face was any indication. “I want to so much, but not until it’s right.”

“What, you want to wait til prom night? Need me to buy you a corsage?” Dean pushed his way back into Castiel’s space and ran his hand down Castiel’s side.

“I doubt a high school dance will have any effect on my decision to sleep with you,” Castiel said with difficulty. It was hard to concentrate with Dean trying to suck a mark into his neck, but he finally shoved Dean far enough away to speak coherently. “I want it to be right,” he said again.

Dean pulled back and looked at him skeptically. “When will it be right?” he asked.

“When you love me,” Castiel said simply. “When you know you want me, for keeps.”

Dean grinned at the expression, then looked down at his hands, still held tightly in Castiel’s. “What if I’m never sure?” he asked. “I’m not exactly good at this relationship stuff, you know.”

“I will wait,” Castiel said. “I’ll wait as long as it takes, and if you never love me the way I love you, I will still want to be with you in whatever way you will allow.”

“Jesus,” Dean said, eyes wide. “Okay, um, maybe we’d better call it a night.”

Castiel sighed a little at his self-imposed rule, but stood after pressing one last kiss to Dean’s mouth. “I will see you again soon,” he said, and left. If he lingered outside the room to watch through the wall as Dean sat on the bed and pressed his fingers against his kiss-swollen lips, well, no one had to know about it.

 

**4\. Sometimes actions speak louder than words, especially when you’re naked**

 

A week later, Castiel found himself entirely engrossed in the movie playing on the small motel room TV set. He was enjoying it so much that he almost forgot about the man lying next to him on the bed until Dean heaved a sigh and jabbed his fingers into Castiel’s side.

“Dean?” Castiel asked, when no explanation appeared forthcoming. “Is something wrong?”

“You haven’t made a move on me in days,” Dean complained. “I’m starting to feel unwanted, man. Making out is what crap movies like this were made for, anyway.”

Castiel frowned. “I like this movie,” he said, “and I will not make a move on you until you’re prepared for what that means.”

“First, this movie sucks. Second, you aren’t going to, uh, do anything weird to me, right? If we do this thing?”

“Define weird,” Castiel requested, because one could never be too careful when it came to Dean.

“Like, start some kind of strange angelic mating ritual? Lay an egg or break out a few tentacles? Or go into pon farr?” Dean grinned. “Well, maybe that last one’s okay.”

Turning onto his side, Castiel tried his best smile, thought better of it, and settled for looking intent. “Nothing like that,” he said. “I want everything we have now, with more sex.”

“Hey, I never had a problem with the sex part!” Dean interjected, and Castiel glared at him.

“I also want an acknowledged exclusive attachment of a romantic nature,” he said.

Dean groaned. “God, you’re going to make me say it, aren’t you?”

He couldn’t help the smirk that appeared on his face at that. “Yes,” he replied, “I want to hear you say it.”

“Fine,” Dean growled, moving to straddle Castiel, who let Dean pin his hands to the bed. “I want you,” Dean said in a low voice. “I’m gonna want you for pretty much forever, is that okay with you?”

Castiel felt a sharp burst of joy at Dean’s words. “Yes,” he said, pulling Dean down within reach of his mouth. “That is more than okay with me.”

They kissed until Castiel no longer cared that he was missing the movie, and this time when Dean reached down to take him in hand, Castiel let it happen. He also helpfully removed all of their clothing with a pass of his hand, and then returned the favor as soon as he could, determined that Dean would never be able to complain about a lack of physical satisfaction again.

 

**5\. Do not let your chosen Winchester notice how indispensable you’ve become until it’s too late**

 

The day Dean realized that Castiel and Sam had been taking turns sitting in the front seat, they had just finished cleaning out a nest of vampires. Castiel had procured the necessary dead man’s blood, and let Dean talk him into being backup so that Sam and Dean could kill all the vampires themselves. He had watched as they easily moved through the old barn that held the nest, beheading each vampire and working seamlessly as a team.

Finished, they all walked to the Impala and Sam nodded to Castiel. “Your turn, man,” he said, opening the back door.

“You need to stretch your legs,” Castiel argued. “I’ll take my turn next time.” He ducked into the back in the seat behind Dean, who sat with his hands frozen on the steering wheel. Sam slid into the front, pushing his legs out into the spacious area in front of his seat gratefully.

“Oh my god,” Dean said. “We live together.”

Castiel met Dean’s gaze in the rear view mirror. “Well, not precisely,” he said, wondering why Dean seemed so shaken. “I don’t technically live anywhere, and neither do you.”

Sam laughed quietly. “He means the car, Cas.”

Of course – the Impala was the closest thing to a home that Dean had, and now Castiel spent almost as much time in it as Dean and Sam. He looked at Dean.

“We live together, and you buy groceries for me, and get me dead man’s blood, and cherry pie when you think I need a pick-me-up, and I buy clothes for you sometimes even though you don’t need them, and I told you I loved you when neither of us were naked, and oh my god, I’m married,” Dean said in a panicked rush.

Sam laughed again, a loud wheezing noise this time, while Castiel stared huffily at Dean.

“You did say forever, Dean,” he said. “It’s not like this should be a surprise to you.”

Dean shook his head and the manic shine left his eyes. He turned in the seat and grabbed Castiel’s hand. “Sorry, babe,” he said. “Sometimes it takes me a while to catch on to these things.”

Castiel pressed his fingers around Dean’s. “It’s okay,” he replied fondly.

Sam snorted then and rolled his eyes, so Dean let go of Castiel’s hand to smack Sam, and drove the whole way back to the motel pouting, while Sam smirked and laughed unrepentantly. Castiel was much too happy to notice anything beyond the occasional glimpse of Dean’s eyes in the mirror.

**Works inspired by this one:**

  * [[Podfic of] Castiel’s Guide to Wooing a Winchester](https://archiveofourown.org/works/1146529) by [exmanhater](https://archiveofourown.org/users/exmanhater/pseuds/exmanhater)




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